Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
The dipole moments of the Z and E isomers of O-methylbenzohydroximoyl cyanides [ArC(CN)=NOCH3, Ar = C6H5 and 4-NO2C6H4], the Z isomers of benzohydroximoyl cyanides [ArC(CN)=NOH, AR = C6H5 and 4-NO2C6H4] and the Z isomers of O-benzoylbenzohydroximoyl cyanides [ArC(CN) = NOCOC6H5, Ar = C6H5 and 4-NO2C6H4] were measured. An analysis of these dipole moments indicates that anti delocalization from the OCH3 (OH) group has a small but significant effect on the overall direction and magnitude of the dipole moment. Semi-empirical molecular orbital calculations at the MNDO level support this proposal. The x-ray crystal structure of (Z)-O-methyl-p-nitrobenzohydroximoyl cyanide was carried out to confirm the configuration of the compound.
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